Composition for lubricating and softening textile fibers



Patented Feb. 8, 1944 UNITED STATES PATENT OFFICE COMPOSITION FORSOFTENING LUBRICATING AND TEXTILE FIBERS Maurice J. Kelley, Newark, andEdwin A. Robinson, Ohatham,

N. 3., asslgnors to National Oil Products Company, Harrison, N. J., acorporation of New Jersey No Drawing. Application August 22, 1939,Serial No. 291,34e

21 Claims. (CL 252-8.8l

sions thereof, the low water dispersibility of these amides renders themsomewhat disadvantageous for use in this connection. While it has beenproposed to solubilize amides of polyamines by treatment with acids, ithas been found that in many cases the solubilization accomplished bysuch treatment i not sufficient to enable these amides to besuccessfully applied to textiles in the form of aqueous dispersionsthereof.

It has also been, proposed to employ amides prepared by reactingmonoethanolamine with fatty materials as textile lubricants andsofteners; such amides, however, are also not as waterdispersible asmight be desired. The use of textile lubricants and softeners comprisingan amide of monoethanol triethylene tetramine has also been suggested;it has been found, however, that the employment of amides of thisaminecauses objectionable yellowing of the textile fibers after thefibers treated therewith have been permitted to stand for a short periodof time.

From the above discussion it will be evident that while a large numberof fatty acid amides of various types have been suggested for use astextile lubricants and softeners, substantially all of these amides havethe disadvantage of either being relatively non-dispersible in water orof causing objectionable yellowing of the textile fiber after the fiberhas been permitted to stand for a short period of time. Therefore, therehas been a constant demand for lubricants and softeners in the textileindustry which do not possess either of the above disadvantages. As yet,however, this demand has not been satisfied.

It is the object of this invention to prepare textile lubricants andsofteners which may be readily applied to textile fibers in the form ofaqueous dispersions thereof, and which do not cause objectionableyellowing of the textile material even after prolonged standing. We havefound that compositions comprising rial without causingany appreciableyellowing of the material even after prolonged standing. In

accordance with our invention textile lubricants:

and softeners are employed which comprise a fatty amide having thegeneral formula moon-m-n-n A in which R1 denotes a fatty acidradicalcontaining more than 5 carbon atoms; R: denotes an organic radicalcontaining not more than 6 carbon atoms having an unsatisfied valence atboth ends thereof and selected from the group consisting of straightchain hydrocarbon radicals, straight chain hydrocarbon radicals having ahydrogen atom replaced by a hydroxyl group, straight chain hydrocarbonradicals and straight chain hydrocarbon radicals having a hydrogen atomreplaced radicals containing a keto grouping; A denotes a radicalcontaining not more than 22 carbon atoms and selected from the groupconsisting of hydrogen, alkyl radicals, alkylol radicals, acyl radicals,and alkyl and alkylol radicals containing an ether or thio etherlinkage; and B denotes a radical containing not more than 22 carbonatoms and selected from the group consisting of alkyl radicals, alkylolradicals, acyl radicals, and alkyl and alkylol radicals containing anether or thio ether linkage, at least one of said R2, A and B radicalscontaining at least one hydroxyl group. The amides of our invention mayeasily be dispersed in aqueous media and the dispersions applied totextile fibers so as to give an excellent feel to the fibers withoutcausing objectionable yellowing of the'fibers even after prolongedstanding. The'preferred products of our invention are those having thegeneral formula R1CONHCH2CH2-NHC2H4OH, since these products may beprepared from the readily available ethanol ethylene diamine, arereadily dispersible in aqueous media and display particularly effectiveproperties when employed as texa certain class of fatty amides may beapplied HN-RzN-B i in which R2, A and B are as above defined, at

-ylaminodimethyl n-pentanol-3.

, also be reacted with amines of the above be reacted with an amine,

least one of said B2, A and B radicals containing at least one hydroxylgroup, with a fatty acid containing more than carbon atoms or with aderivative thereof capable of reacting with amines to form amides. Thus,for example, the following amines have been found to be suitable for usein the preparation of the products of our invention: ethanol ethylenediamine, l-amino 3 methylamino isopropanol, N-ethyl N-ethanol ethylenediamine, N,N diethanol ethylene diamine, isopropanol ethylene diamine,l-amino 3-dimethylamino isopropanol, l-amino 2-ethyl 3-methylaminoisopropanol, l-amino 2-ethyl 3-ethanolamino isopropanol andl-aminodimethyl 5-meth- We prefer to employ ethanol ethylene diamine inthe practice of our invention since this amine is readily available andfurnishes excellent water-dispersible textile lubricants and softenerswhen treated with fatty acids or their derivatives. It is to beunderstood, however, that other amines having the above generic formulamay also be employed in the practice of our invention.

The fatty compounds with which the above amines may be reacted inaccordance with our invention may be any fatty acid having more than 5carbon atoms or a derivative thereof capable of reacting with amines toyield amides. Thus, for example, fatty acids such as stearicacid,-capric acid, oleic acid, coconut oil fatty acids or mixtures:thereof, and fatty acid derivatives such as olive. oil, coconut oil, codoil, sperm oil, japan wax. methyl oleate and glyceryl monoor di-stearatemay be employed to react with the amines. Naphthenic acids or theiresters may type to yield amides suitable for use in accordance with ourinvention, and we intend to include such reaction products within thescope of the term fatty amides" since the properties of the naphthenicamides are entirely similar to the properties of the amides formed byreacting the mines with fatty acids or their derivatives. We

have found. that triglycerides of fatty acids containing more than 5carbon atoms. e. g., coconut oil, teaseed oil. hydrogenated soy-bean oiland the like, react easily with the amines and yield amides havingsomewhat superior softening properties than those obtained by reactingthe corresponding free fatty acids with the amines; hence we prefer toemploy triglycerides of fatty acids having more than 5 carbon atoms asthe fatty compounds reacted with the amines.

The reaction of the amine with the fatty compound may be carried outmany suitable manner. The amount of fatty compound employed per mol ofamine will vary depending upon the nature of the fatty compound used:thus it a fatty acid is to approximately equimolecular amounts of theacid and amine may be employed, whereas if a triglyceride such ascoconut oil is used, approximately one-third of 8. mol of triglycerideper mol of amine may be employed. The temperature of the reaction mayvary between about 100 C. and the boiling point of the amine, butpreferably temperatures between about 125 C. and about 175 C. areemployed. The reaction is preferably carried out at atmosphericpressure, but pressures below or above atmospheric may be used ifdesired. The reaction time may vary widely depending upon the particularingredient employed; generally the reaction time will be between about 2hours and about 48 hours. The products obtained from the reaction may berecovered in any suitable The fatty amides of our invention. may beapplied to textilev materials in any sniiablema-nner.

Because of the fact that these amides are dis-' persible in aqueous.media, we have: found. it most advantageous; to apply these amides: to:-textile fabrics in thei'ormof aqueous dispersions: thereof.- Thesedispersions may be prepared in a variety of ways. We have: found; that:aqueous dispersions of the amides: of our invention are mostadvantageously prepared by mixing the: amide, preferably in liquidcondition, with a dilute aqueous solution of an acid such as aceticacid, hydrochioric acid or lactic acid, whereby stable dispersions ofthe amides are formed immediately. dispersions. may containany suitableamount of the fatty amide. but;- we. prefer to: employdispersionscontaining'betweerr about 0.001% and about 5%; thereof; thus it wiltbeaobserved that dispersions containing. very small amounts of the amidesofour: invention arecapable of imparting. an excellent finish to textilefabrics. In many cases it may be desirable to prepare. relativelyconcentrated dispersionsofithe amide, e. g., dispersions containing 25%thereof, and then dilute. the dispersionsthus: prepared tothe desiredconcentration before. use; this method of preparing; the dispersions;is: advantageous when itis desired to store: or: ship thedispersionsprior to use. Textile:- i'abrics. treated with the amides ofourinvention show no objectionable yellowing even after prolongedperiods of time.

It is to be understood that while it is preferred to apply the amides:of our invention to textile fabrics in the form of aqueous dispersionsthereof, these amides maybe applied in any other suitable mannerwithoutv interferin with the excellent softness, pliabili'ty and drapewhich they impart to the fabrics.

The following. examples are illustrative of our invention.

. immersed in this dispersion for 10 minutes at a temperature of about40 C. At the end of this time, the fabric was removed, squeeze-rolled,dried and ironed lightly. The fabric was. found and. drape, and did notyellow even after prolonged, standing.

Example I! 680 parts of coconut oil and 156 parts of ethanol ethylenediamine were mixed and the mixture heated at a temperature between aboutC. and about C. for 12 hours. A. light tan solid dispersible in waterwas obtained. This product was melted and hot water added thereto untilan 0.015% dispersion of the amide was formed. This dispersion was thenapplied to rayon fabric as described in Example I, whereby a fabric wasobtained having excellent softness and drape, and which did not yelloweven after prolonged standing.

Example III 28 parts of oleic acid and 10 parts of ethanolethylene-diamine were mixed and heated at a temperature between about150 C. and about Amounts are given in parts: by weight.

1 170 C. for 12 hours. The resulting product was melted and 175 parts ofa warm 4% acetic acid solution were added thereto. This solution wasthen diluted until an 0.015% dispersion of the amide was formed and thisdispersion applied to rayon fabric as described in'Example 1, whereby afabric was obtained having excellent softness and drape, and which didnot yellow even after prolonged standing.

Example 1v 33 parts or castor oil and parts of ethanol ethylene diaminewere mixed and the mixture heated to a temperature between about 150 C.

' and about 170 C. for 8 hours, whereby 'a yellow liquid was obtained.This liquid was mixed with 205 parts of a hot 4% acetic acid solution,and the resulting solution diluted so as to form an 0.015% dispersion ofthe amide. This dispersion was applied to rayon fabric as described inExample I, whereby a fabric was obtained hav ing excellent softness anddrape, and which did not yellow even after prolonged standing.

Exampte V terpreted as illustrative and not 1.. a limiting sense.

Having described our invention, what'we claim as new and desire tosecure by Letters Patent is".

1. A composition of matter comprising anamide which is the condensationproduct of a hydroxy-alkylated polyamine with a glyceride containingonly substantially saturated non-hydroxylated fatty radicals.

2. A composition of matter comprising" an amide which is thecondensation product of a polyamine of the type in which at least one ofthe amino groups contains a hydroxy-alkyl group, with a glyceridecontaining only substantially saturated non-hydroxylated fatty radicals.

3. A composition of matter comprising an amide which is the condensationproduct of v monoethanol-ethylene-diamine with a glyceride '74 parts ofteaseed oil and 26 parts of ethanol ethylene'diamine were mixed and themixture heated at a temperature between about 150 C. and about 170 C.for 8 hours. The product was a light tan solid. This product was meltedand- 205 parts of a hot 4% acetic acid solution were added thereto. Theresulting solution was diluted untilan 0.015% dispersion of the amidewas formed. This dispersioirwas applied to rayon fabric. as described inExample I, wherebya fabric was obtained having excellent softness anddrape, and which did not yellow even after prolonged standing.

Example VI 31 parts of hydrogenated soybean oil and 11 parts of ethanolethylene diamine were mixed and the mixture heated at a temperaturebetween about C. and about C. for 8 hours. The resulting solid wasmelted and 205 parts of a hot 4% acetic acid solution were addedthereto. The solution thus obtained was then diluted until an 0.015%dispersion of the amide was formed.

- This dispersion was then applied to rayon fabric as described inExample 1, whereby a fabric was obtained having excellent softness anddrape, and

which did not yellow even after prolonged standv ing.

It will be evident from the above description that our inventionprovides novel textile lubricants and softeners having properties whichmake them superior to lubricants and softeners heretofore employed.Therefore, our invention will be of great interest to those engaged inthe finishing of textile materials.

The products of our invention may be further treated, if desired, toproduce substances having desirable properties. For example, the amidesmay be sulfated or fosphated to yield wetting, dispersing andemulsifying agents, or they may be treated with acetic anhydride toyield products having excellent detergent and dispersing properties. Ournovel products may also be treated in a variety of other manners knownto the art so as to yield useful substances.

Since certain changes may be made in-the above products and differentembodiments of the invention could be made without departing from thescope thereof, it is intended. that all matter contained in the abovedescription shall be inethanol-ethylene-diamide with coconut oilglycerides.

'7. A composition of mat er comprising amides which are the condensatioproducts of monoethanol-ethylene-diamine with hydrogenated soyabean oilglycerides.

8. Acomposition of matter for lubricating and softening textile fibersconsisting of an aqueous dispersion, in dilute acid solution, of anamide which is the condensation product of a hydroxyalkylated polyaminewith aglyceride containin only substantially non-hydroxylated fattyradicals.

9. A composition of matter for lubricating and softening textile fibersconsisting of an aqueous dispersion, in dilute acid solution, of anamide which is the condensation product of a polyamine of the type inwhich at least one of the amino groups contains a hydroxy-alkyl group,with a glyceride containing only substantially non-hydroxylated fattyradicals.

10. A composition of matter for lubricating and softening textile fibersconsisting of an aqueous dispersion, in dilute acid solution, of anamide which is the condensation product of monoethanol-ethylene-diaminewith a glyceride containing only substantially non-hydroxylated fattyradicals.

11. Compositions of matter for lubricating and softening textilefibersconsisting of aqueous dispersions, in dilute acid solutions, of amideswhich are the condensation products of a hydroxy-alkylated polyaminewith coconut oil glycerides.

12. Compositions of matter for lubricating and softening textile fibersconsisting of aqueous dispersions, in dilute acid solutions, of amideswhich are the condensation products of a hydroxy-allgvlated polyaminewith hydrogenated soyabean oil glycerides.

-13. Compositions of matter for lubricating and softening textile fibersconsisting of aqueous dispersions, in dilute acid solutions, of amideswhich are the condensation products of monethanolethylene-diamine withcoconut oil glycerides.

14. Compositions of matter for lubricating and softening textile fibersconsisting of aqueous dispersions, in dilutei acid solutions, of amideswhich are the condensation products of monoethanolethylene-diamine withhydrogenated soya-bean oil glycerides.

15.- A composition of matter consisting of an aqueous dispersion, indilute acid solution, of an amide which is the condensation product of ahydroxy alkylated polyamindwith a glyceride containing onlysubstantially saturated, nonhydroxylated fatty radicals.

16. A composition of matter consisting of an aqueous dispersionyiindilute acid solution, of an amide which is the condensation product of apolyamine of the type in which at least one of the amino groups containsa hydroxy-alkyl group,

' with a glyceride containing only substantially saturated,non-hydroxyiated fatty radicals.

17. A composition of matter consisting of an 20 aqueous dispersion, indilute acid :solution, of an amide which is the condensation product ofmonoethanol-ethylene-diamine with a glyceride containing onlysubstantially saturated, n onhydroxylated fatty radicals.

18, Compositions of matter consisting of aqueous dispersions, in diluteacid solutions, of amides which are the condensation products of ahydroxy-alkylated polyamine with coconut oil glycerides. Y

19. Compositions of matter consisting of aqueous dispersions, in diluteacid solutions, of amides which are the condensation products of ahydroxy-alkylated polyamine with hydro- I genated soyabean oilglycerides.

20. Compositions of matter consisting of aqueous dispersions, in diluteacid solutions, of amides which are the condensation products ofmonoethanol-ethylene-diamine with coconut oil glycerides.

21. Compositions of matter consisting of aqueous dispersions, in diluteacid solutions, of

amides which are the condensation products ofmonoethanol-ethylene-diamine with hydrogenated soyabean oil giycerides.

MAURICE -J. KELLEY. EDWIN A. ROBINSON.

CERTIFICATE or consscrron.

Patent n0; 2,5 i0,8e1.

musics J. KELLEY, ET AL.

February 8, 191414..

" It is hereby certified that error appears in the printed specificationof the above numbered patent requiring correction as follows 3' Page 5,first column, line 61;, for "fosphated" read --phosphat ed--; line 52,claim 6, for "diamide" read --dianine-;

and second column, lines i 1 and 5 claims 8, 9 and lo'respectively,after "substantially" insert -satura ted--; and that the said LettersPatent should be read with this correction therein that the same mayconform to the record of the case in the Patent Ofri ce.

(Seal) si ed and sealed this 25th day of April, A. D. 191 h.

Leslie Frazer Acting Commissioner of Patents.

CERTIFICATE OF commoner. Pateot No; 215 40381. Febmary 8, 19M" mus cs J.KELLEY, m AL.

I It is hereby certified that error appears in the printed specificationof the above n umbered patent requi ring correction as follows Page 5,first column, line 61;, for "fosphated" read --phosphat ed--; and secondcolumn, line 32, claim 6, for "diamide" read "(aminelines b5, 51 and 5claims 8, 9on6. IO-respectively, after "substantially" insert"saturated"; and that the said Letters Patent should be read with thiscorrection therein that the same may comom to the record 01 the case inthe Patent 01- rice.

Signed and sealed this 25th day of April, A. 1). 191m.

Leslie Frazer (Seal) Acting Commissioner of Patents.

